Synthesis of homofascaplysin C and indolo[2,3-a]carbazole from ditryptophans

被引：29

作者：

Carter, DS ^{[1
]}

Van Vranken, DL ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 23期

关键词：

D O I：

10.1021/jo9909249

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2,2'-biindole core of ditryptophan cross-links is prominent in the fascaplysins and the indolocarbazole glycoside natural products. N-Acyliminium ions derived from the C-terminus of ditryptophan peptides cyclize in one of two modes: N-alkylation or C-alkylation. The surrounding peptide offers some control over the course of the cyclization and allows the preparation of homofascaplysin C or indolo[2,3-alpha]carbazole. These targets are modest, but they are generated through carbocyclic intermediates rich in stereochemistry, and decidedly non-peptide in character.

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页码：8537 / 8545

页数：9

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